1H-1,2,4-Triazole → HCID 178509721, compound

HRID 2259471Notes

Reaction equation

HRID 2259471 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(Cl)(Cl)Cl.C(#N)C>[NH:11]1[CH:15]=[N:14][C:13]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=2)=[N:12]1

Participants

5

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 178509721HCID 178509721, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution containing alpha-bromo-4-tolunitrile (19.6 g) and 1,2,4-triazole (30.5 g) in a mixture of chloroform (250 mL) and acetonitrile (50 mL) is stirred at reflux for 15 hours. The solution is cooled and washed with 3% aqueous sodium bicarbonate (200 mL) and the organic solution is then dried (MgSO4) and evaporated. The residue is chromatographed on silica gel (300 g). Elution with chloroform/isopropanol (10:1) affords 4-[1-(1,2,4-triazolyl)methyl]-benzonitrile, m.p. 77°-79°, which forms a hydrochloride salt, m.p. 200°-205°, when its solution in ethyl acetate is treated with ethereal HCl.

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureThe solution is cooled
  3. washwashed with 3% aqueous sodium bicarbonate (200 mL)
  4. dry with materialthe organic solution is then dried (MgSO4)
  5. customevaporated
  6. customThe residue is chromatographed on silica gel (300 g)
  7. washElution with chloroform/isopropanol (10:1)

Sources & evidence

ORD record
ord-ebeb37b02cd94ecf8a30acd0ce49a672
Source dataset
uspto-grants-1995_12
Patent number
US05473078

Reaction notes

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